Process for producing all trans-form polyprenols

Abstract

An all trans-form polyprenol is obtained by; (A) subjecting a 3,7-dimethyl-6-hydroxy-7-octen-1-ol derivative to five-carbon lengthening reaction m-times which comprises reacting with 2-methyl-3,3-dimethoxy-1-butene and reducing the carbonyl group of the resulting compound, to obtain an allyl alcohol derivative; (B) halogenating the hydroxyl group of the allyl alcohol derivative to convert it to form an allyl halide derivative; (C) allowing the allyl halide derivative to react with a polyisoprenyl sulfone derivative to form a sulfonated polyprenol derivative; and (D) subjecting the sulfonated polyprenol derivative to desulfonylation to obtain the all trans-form polyprenol.

What is claimed is: 
     
       1. A process for producing a all trans-form polyprenol represented by Formula (1): ##STR67## wherein Y and Z each represent a hydrogen atom, or combine to form a carbon--carbon bond; said process comprising the steps of: (A) subjecting a compound represented by Formula (2): ##STR68##  wherein Y and Z are as defined above, and A represents a protective group of the hydroxyl group; to five-carbon lengthening reaction m-times which comprises reacting the compound of Formula (2) with 2-methyl-3,3-dimethoxy-1-butene and reducing the carbonyl group of the resulting compound, to obtain a compound represented by Formula (3): ##STR69## wherein Y, Z and A are as defined above, and m represents an integer of 1 to 4;       (B) subjecting the compound represented by Formula (3), to halogenation to convert it to a compound represented by Formula (4): ##STR70##  wherein Y, Z and A are as defined above, and X represents a halogen atom; (C) allowing the compound represented by Formula (4) to react with a compound represented by Formula (5): ##STR71##  wherein m is as defined above, and R 1  represents an alkyl group or an aryl group; to obtain a compound represented by Formula (6): ##STR72## wherein Y, Z, A, m and R 1  are as defined above; and (D) subjecting the compound represented by Formula (6) to desulfonylation and deprotection to obtain the all trans-form polyprenol represented by Formula (1).     
     
     
       2. The process according to claim 1, wherein said compound represented by Formula (2), the starting material in the step (A), is obtained through the following steps (a) to (c) of: (a) introducing a protective group A to the hydroxyl group of a compound represented by Formula (70): ##STR73##  wherein Y and Z each represent a hydrogen atom, or combine to form a carbon--carbon bond; to obtain compound represented by Formula (71): ##STR74## wherein Y and Z are as defined above, and A represents a protective group of the hydroxyl group;     (b) subjecting the compound represented by Formula (71) to epoxydation to obtain a compound represented by Formula (72): ##STR75##  wherein A is as defined above; and (c) rearranging the epoxy group of the compound represented by Formula (72) to an allyl alcohol to convert the compound to the compound represented by Formula (2).   
     
     
       3. The process according to claim 1, wherein said Y and Z each represent a hydrogen atom. 
     
     
       4. The process according to any one of claims 1 to 3, wherein in the step (A) the carbonyl group is reduced using an aluminum alkoxide and a secondary alcohol. 
     
     
       5. A process for producing a compound represented by Formula (101): ##STR76## wherein X represents a halogen atom; Y and Z each represent a hydrogen atom, or combine to form a carbon--carbon bond; A represents a protective group of the hydroxyl group; and n represents an integer of 1 or more; said process comprising the steps of: (A') subjecting a compound represented by Formula (2): ##STR77##  wherein Y, Z and A are as defined above; to five-carbon lengthening reaction n-times which comprises reacting the compound of Formula (2) with 2-methyl-3,3-dimethoxy-1-butene and reducing the carbonyl group the resulting compound, to obtain a compound represented by Formula (103): ##STR78## wherein Y, Z, A and n are as defined above; and (B') subjecting the compound represented by Formula (103), to halogenation to obtain the compound represented by Formula (101).     
     
     
       6. The process according to claim 5, wherein said Y and Z each represent a hydrogen atom. 
     
     
       7. The process according to claim 5 or 6, wherein in the step (A) the carbonyl group is reduced using an aluminum alkoxide and a secondary alcohol. 
     
     
       8. A process comprising treating a compound represented by Formula (202): ##STR79## wherein p and q each represent an integer of 0 or 1 or more; Y and Z each represent a hydrogen atom, or combine to form a carbon--carbon bond; R 1  represents an alkyl group or an aryl group; and A represents a protective group of the hydroxyl group; with an alkali metal and a polycyclic aromatic compound to produce a compound represented by Formula (201): ##STR80## wherein p, q, Y and Z are as defined above; and R 2  represents a hydrogen atom or the same protective group of the hydroxyl group as that represented by A.   
     
     
       9. The process according to claim 8, wherein said Y and Z each represent a hydrogen atom.